


These Heels Were Made for Tripping

by yoursourwolfisshowing



Category: Teen Wolf (TV)
Genre: Drag Queen, First Time, M/M, Pining, Romance, sassy!Stiles, virgin!stiles
Language: English
Status: Completed
Published: 2013-01-02
Updated: 2013-01-02
Packaged: 2017-11-23 08:39:53
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,298
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/620194
Author URL: https://archiveofourown.org/users/yoursourwolfisshowing/pseuds/yoursourwolfisshowing
Summary: <blockquote class="userstuff">
              <p>Stiles loved drag queens. Maybe he even loved drag queening. Derek liked Stiles in drag too, apparently.</p>
            </blockquote>





	These Heels Were Made for Tripping

So maybe Stiles shouldn’t have let the girls take him out for a “night on the town.” Maybe. And by girls, he means the drag queens he befriended that night at Jungle. Not that they weren’t great, they were, but if he had to guess at the beginning of last year, he did not think he would be spending time with two sassy women hanging on to his every word. It. Was. Awesome.

Except for the part that he was in “hooker heels,” had eyeliner and lipstick on, ridiculous shirt made for people with boobs (which he had none of), and was pretty sure his dick was going to fall off from how tight his pants were. How Lydia wore heels every day, he would never be able to fathom. They bit at the sides of his toes, he was pretty sure he was wobbling more than ever, and that was not good at all since he was clumsy already. Each time he tripped, one of them would laugh and pick him back up and pat him on the ass.

Shrugging off the thought of them wanting Stiles, he continued down the street with them ignoring the catcalls. Okay, so maybe only a few he ignored and those were by not so attractive men. 

Rounding the corner Stiles bumped into Danny and blanked. “Uh… uh… Hi, Danny ole’ buddy ole’ pal!”

Danny blinked and looked at Stiles’ outfit and snickered. “What are you doing, Stilinski?”

Queenie, the head of the posse glared at Danny and shot back, “He’s out with us, darling! Why don’t you join? We could always use a few more bottoms in our group.” Winking, Queenie hooked her arm into Stiles’ and dragged him off down the street, Stiles still in disbelief.

While they were walking away, Danny yelled, “What’s your drag name, Stiles?!”

“Sugar Spice!” Candy hollered back to him.

Stiles groaned and let himself be pulled off. They were so embarrassing, but it was always destined to be a good night. Throwing his arms around Queenie’s and Candy’s shoulders he said, “So gals, where we going tonight?”

“Coffee shop!” Queenie replied and continued strutting while tangling her fingers in Stiles’.

“That’s pretty tame… even for you guys. Shouldn’t you be in Jungle sacrificing virgins to the Gods?”

Candy snickered and bumped her hip in Stiles’. “Darling, that would mean we’d sacrifice you.”

“…shit.”

Continuing, Candy said, “We have to work on de-virginizing you! With those heels, I doubt it’ll be long, but it would help to have someone to speed it up a bit.”

As they walked into the coffee shop, the all sat down at the bar, quickly telling their orders to the barista. Queenie asked, “Do you have anybody in mind?”

Stiles nervously picked at his nails. “Well, there’s one person, but I doubt they’d even notice me unless I tackled them or acted stupid.”

Candy rounded on Stiles, interested. “Ooh, is it that hottie you were with at Jungle last time?”

“Scott?”

“Yeah, yeah!”

Stiles snorted and shook his head. “Never! He’s my bro. It’s someone else. Someone… older?”

“Ooh, how much older?”

“Few years, give or take… I haven’t been able to look in the police report.”

“And he’s a convict?”

“Exonerated since the charges were false!”

As the drinks were placed in front of them, Stiles noticed that a number was on his. Well that had never happened before. Awesome. Winking at the barista he turned to Queenie. “Help! I don’t know what to do, like ever around this person.”

Queenie sighed and patted Stiles’ on the back, taking a sip of her frappe before speaking slowly. “Well… I’d love to tell you be yourself, but that’s not always the case. Wear this around them, see how it goes!”

Stiles nodded. Maybe he could do that. The pack would probably die laughing, but seeing Derek’s reaction would be gold. “What else though? Like… is there anybody about me that I could work on?”

Both of the girls said at once, “Babbling.”

Stiles flailed his arms around almost knocking over his coffee. “Come on! Like that could ever happen! …Although, that’s where a lot of issues happen because I babble and don’t listen and ugh, I’m doing it again aren’t I?” 

They nodded and each went back to pursing their lips and sipping their drinks. Stiles groaned and slammed his head on the bar. There was no way he could ever get sex god Derek Hale to want him. Queenie jabbed him and whispered, “Hottie at 5 o’clock, think they’re checking you out.”

Trying not to be obvious, Stiles turned to the side and almost fell out of his chair. Derek. Was here. In the coffee shop with him. Whipping a pen out of his pocket he scribbled on Queenie’s napkin, that’s him! Queenie’s eyes widened and she said, “Boy, you have your work cut out for you.” Passing the note to Candy, she nodded in agreement.

“Tell me about it.”

Derek walked up behind Stiles and waited for the barista. Deciding to tease Stiles he said, “Tell you about what, Stiles?”

Eyes widening Stiles stuttered out, “N-Nothing.”

“You sure? I mean, I’m here if you have any questions or anything.”

Spinning around, Stiles met Derek’s eyes and snarked back, “What could I have questions about that you could possibly answer?”

Derek moved forward and put his arms on either side of Stiles. “Oh, I don’t know. Maybe how to gloss your lipstick right so it doesn’t smear when you drink coffee or get all over the cup.”

Stiles’ mouth dropped open and he opened his mouth to reply a few times, but nothing happened. “Uh…” Crap, now he was imaging Derek in lipstick. And heels. Not a good time. BAD PENIS, GO DOWN.

Derek smirked and leaned back off of him and grabbed Stiles’ coffee and began walking out of the shop calling over his shoulder, “Here if you need me, Sugar Spice.”

Queenie and Candy shoved Stiles out of his chair gesturing frantically to the door. Nodding, Stiles tripped over himself while running out of the shop to catch up to Derek. After running down half the block Stiles’ called out, “Wait, wait! I can’t! I can’t do this. Ugh, heels are the devil,” while trudging the last few steps to Derek.

Derek paused and turned around waiting on Stiles. “Well, you coming?”

“What do you promise me if I come, coffee stealer.”

“What was it that Candy and Queenie called it, de-virginizing?”

Stiles gaped once more and picked up his pace. “…How did you know?”

Smirking, Derek wrapped his arm around Stiles’ waist and said, “Danny may or may not have texted me: Stiles in drag, questioning how I feel about him. I had to make sure it was true.”

“Yeah okay. You just want my body.”

Derek leaned down and nuzzled into Stiles’ neck. “Maybe I do. Maybe I just want you.”

Derek Hale never failed to surprise Stiles. He would act like he hated him some days and now, ugh, now he was freaking nuzzling his neck? Jesus, what was the world coming to?! Stiles grinned and started dragging Derek down the street to his car parked at the corner. “Come on then! We need to get started, because this could take a while.”

“Who said it would happen tonight?”

“Me.”

“You’re much more confident in drag aren’t you?” As they continued walking to the car, Stiles tried to ignore how nervous he felt. They were silence for a few minutes, which was rare, until they reached the Camaro. Then, Derek squeezed him once around the waist and whispered in his ear before heading over the driver’s side, “Maybe I’ll even let you keep the heels on.”

Needless to say, Stiles loved drag queens.


End file.
